Teacher Notes
|
||||||
---|---|---|---|---|---|---|
Teacher Notes![]() Analysis of Over-the-Counter DrugsStudent Laboratory KitMaterials Included In Kit
Acetaminophen tablets, 20*
Acid Controller Complete tablets, 4* Alka-Seltzer® tablets, 10* Antacid generic tablets, 20* Aspirin tablets, 20* Bufferin® tablets, 20* Excedrin® tablets, 20* Hydrochloric acid solution, HCl, 0.5 M, 125 mL Ibuprofen tablets, 20* Iron(III) nitrate solution, Fe(NO3)3, 0.2 M, 125 mL Universal indicator solution, 100 mL pH indicator paper, 2 vials of 100 pieces Pipets, Beral-type, 60 Toothpicks for stirring, box of 250 Universal indicator color chart *OTC drug samples Additional Materials Required
Cotton swabs (for cleaning wells)
Mortar and pestle Reaction plate, 24-well Sheet of white paper Spatula Test tubes, 5 Test tube rack Vial or test tube (for unknown sample) Prelab PreparationTo prepare unknown samples of the OTC drugs: Use a mortar and pestle to grind up an OTC drug tablet until it is fully powdered. Place one or two small scoopfuls of the powder in a vial or test tube. Label the test tube or vial with an unknown number. Distribute an unknown sample to each group of students. Safety PrecautionsDo not allow students to ingest any of the over-the-counter drug samples during this laboratory. The samples are for laboratory use only, have been stored with other non–food-grade laboratory chemicals and are not meant for human consumption. Hydrochloric acid solution is toxic by ingestion and inhalation and is corrosive to skin and eyes. Iron(III) nitrate solution may be a skin/tissue irritant. Universal indicator solution is a flammable, alcohol-based solution. Avoid contact of all chemicals with eyes and all body tissues. Wear chemical splash goggles, chemical-resistant gloves and a chemical-resistant apron. Please review current Safety Data Sheets for additional safety, handling and disposal information. DisposalPlease consult your current Flinn Scientific Catalog/Reference Manual for general guidelines and specific procedures, and review all federal, state and local regulations that may apply, before proceeding. The contents of the wells of the reaction plates may be rinsed down the drain with plenty of water according to Flinn Suggested Disposal Method #26b. Remaining OTC drug samples can be disposed of in the solid waste disposal according to Flinn Suggested Disposal Method #26a. Teacher Tips
Further ExtensionsThis lab can be easily extended to a cross-curricular creative writing activity. Combine scientific qualitative analysis with writing by having students develop a “crime scene” scenario dealing with OTC drugs. Correlation to Next Generation Science Standards (NGSS)†Science & Engineering PracticesAnalyzing and interpreting dataPlanning and carrying out investigations Disciplinary Core IdeasMS-PS1.A: Structure and Properties of MatterMS-PS1.B: Chemical Reactions HS-PS1.A: Structure and Properties of Matter Crosscutting ConceptsPatternsPerformance ExpectationsMS-PS1-2. Analyze and interpret data on the properties of substances before and after the substances interact to determine if a chemical reaction has occurred. Sample Data{11856_Data_Table_1}
{11856_Data_Table_2}
Answers to QuestionsPart I Questions
ReferencesEby, D. and Tatum, R. The Chemistry of Over-the-Counter Drugs; Flinn Scientific: Batavia, IL, 1989. Recommended Products
|
||||||
Student Pages
|
---|
Student Pages![]() Analysis of Over-the-Counter DrugsIntroductionLearn to analyze and identify over-the-counter (OTC) drugs including common pain relievers, such as aspirin and acetaminophen, and antacids, such as Alka-Seltzer®. Test physical and chemical properties of actual OTC drug samples and then use test results to analyze unknown pain reliever and antacid samples. Concepts
BackgroundA drug is a chemical used medicinally for treating diseases and injuries. The term “drug,” however, often carries with it the connotation of narcotics, addiction and crime. Many drugs or medicines are entirely legal, readily available, and are sold as over-the-counter medications without the need for a prescription. Over-the-counter (OTC) drugs include categories of drugs such as pain relievers, antacids, alcohol, caffeine and vitamins. While these OTC drugs are sold legally they, like controlled or prescription drugs, have the ability to cause accidental or purposeful poisoning and even death if taken improperly. Thus it is important that dosage information and precautions printed on the label are strictly followed in order to prevent accidental injury or harm. The first class of OTC drugs tested will be pain relievers—specifically aspirin, acetaminophen, ibuprofen, Bufferin® and Excedrin®. Aspirin, the common or trade name for acetylsalicylic acid, is today’s leading commercial pain reliever. Aspirin acts as an analgesic (pain reliever), an antipyretic (fever reducer) and an anti-inflammatory agent (inflammation reducer). Aspirin is a fairly acidic compound which reacts slowly with moisture from the air to undergo hydrolysis, forming salicylic acid and acetic acid (vinegar), as shown in Equation 1. {11856_Background_Equation_1}
Thus if aspirin is to be stored for several months, it should be kept dry. If the tablets pick up moisture, they may begin to smell like vinegar and become even more acidic. This increased acidity can be very irritating to the lining of the stomach and intestines, causing side effects such as upset stomach, gastrointestinal bleeding, and various allergic reactions. Furthermore, aspirin, as with any drug, must get into the bloodstream in order to do its work. The time it takes for the acetylsalicylic acid in tablet form to enter the blood is limited by the rate at which the tablet disintegrates in the stomach, which is dependent on pH. The higher the pH (less acidic), the faster the tablet disintegrates. For these reasons, some people opt to take a buffered aspirin, which contains aspirin and one or more weak bases. Bufferin® is a brand of buffered aspirin containing aspirin, calcium carbonate, magnesium oxide, and magnesium carbonate. The combination of aspirin and weak bases increases the pH, thus helping with the disintegration of the tablet and hence the absorption of the acetylsalicylic acid into the blood stream. The weak bases in buffered aspirin reduce the acidity that results from the hydrolysis of aspirin in the acidic juices of the stomach; thus, buffered aspirin is found to be less irritating to the stomach lining than aspirin. The acetylsalicylic acid (aspirin) molecule has an ester side chain group, as shown in Figure 1. The ester group hydrolyzes in the presence of water, leaving an alcohol group (–OH) on the benzene ring, or a phenol compound. A chemical test to detect the presence of the phenol group is seen in the reaction with iron(III) nitrate. When a phenol group is present, a distinct violet-colored complex is formed. Therefore iron(III) nitrate is commonly used as a positive indicator test of the phenol group (and thus for aspirin which easily undergoes hydrolysis). {11856_Background_Figure_1_Acetylsalicylic acid-Aspirin}
{11856_Background_Figure_2_Acetaminophen-Tylenol®}
{11856_Background_Figure_3_Ibuprofen-Advil®}
Acetaminophen, a non-aspirin headache remedy, is another important OTC pain reliever. Acetaminophen, which is an acylated aromatic amine as shown in Figure 2, is the active ingredient in Tylenol®. Compare Figures 1 and 2 and notice the similarities and differences between the chemical structures of the two pain relievers. Notice that acetaminophen has an alcohol group (–OH) on the benzene ring, also known as a phenol group. Thus, in the presence of iron(III) nitrate, a distinct violet-colored complex is produced due to the reaction of iron(III) nitrate with the phenol group. Acetaminophen acts as a mild analgesic and antipyretic, but lacks anti-inflammatory properties. Acetaminophen is a less acidic alternative to aspirin for those who have an allergic reaction or who find that aspirin produces stomach disorders. Excedrin® is a combination OTC pain reliever, consisting of equal amounts of aspirin and acetaminophen, and a small amount of caffeine. The caffeine is added as a stimulant to the nervous system and heart, providing a heightened sense of awareness that some people want in a pain reliever. Ibuprofen, another commonly used pain reliever, is the active ingredient in Advil®. Ibuprofen, shown in Figure 3, is another non-aspirin OTC drug. However, like aspirin, ibuprofen acts as an analgesic (pain reliever), an antipyretic (fever reducer) and an anti-inflammatory agent (inflammation reducer). Compare Figures 1, 2 and 3, noticing the similarities and differences among the chemical structures of the three molecules. The second class of OTC drugs tested will be antacids—specifically Alka-Seltzer®, Acid Controller Complete® and a genericant acid containing calcium carbonate. Antacids are chemicals that relieve over-acidity by neutralizing excess acid in the stomach. This excess acid can produce discomforts, commonly called “acid indigestion” or “heartburn,” and possibly gastric ulcers. Antacids promise to provide “prompt relief” of the unpleasant effects of these stomach distresses. Most antacids will not dissolve completely in water and are made to dissolve slowly in the acidic juices of the stomach so carbon dioxide will be given off gradually as the antacid neutralizes excess acid. The stomach’s digestive juices, or gastric juices, contain hydrochloric acid (HCl), which serves to promote digestion of food proteins by the enzyme pepsin in the gastric juices and kill bacteria that enters our digestive system. The stomach lining of a normal adult produces two to three liters of dilute HCl each day to aid in digestion, with a normal stomach pH ranging from 1.0 to 3.0. While the stomach produces a small amount of acid all the time, it can be stimulated to produce more acid in the presence of food. Too much food, certain types of food, or high levels of stress may cause the stomach to respond with an outpouring of acid, thus lowering the stomach pH to the point of discomfort. Most common antacids contain weak bases such as sodium bicarbonate, calcium carbonate, magnesium hydroxide, aluminum hydroxide, or various combinations of these. The basic compounds in the antacids serve to neutralize excess HCl as well asto affect the functioning of the enzyme pepsin. An acid–base neutralization reaction occurs between the base and the acid in the stomach. An effective antacid does not bring the pH of the stomach fluid to complete acid–base neutrality (pH of 7) as this would completely shut down digestion and promote “acid rebound”—an automatic response which floods the stomach with fresh acid. Instead, an effective antacid neutralizes some of the HCl in the gastric juices—enough to relieve the pain and discomfort, yet still allowing for the continuation of normal digestive processes. Carbonate-containing antacids, such as sodium bicarbonate, react with stomach acid to produce a neutral salt and carbonic acid. Carbonic acid is a much weaker acid than HCl and decomposes readily to yield carbon dioxide and water, as shown in Equation 2. Hydroxide-containing compounds, such as magnesium hydroxide, react with the acid to produce its neutral salt and water, as shown in Equation 3. {11856_Background_Equation_2}
{11856_Background_Equation_3}
Alka-Seltzer is a popular antacid and pain relief medicine, containing aspirin, citric acid, and sodium bicarbonate (baking soda). When the tablet is dropped into water, the bicarbonate and the citric acid dissolve, producing the familiar “fizz” from the chemical release of carbon dioxide. Complete Acid Controllers are another common type of antacid, containing a combination of calcium carbonate and magnesium hydroxide. The first types of antacids, such as traditional Tums®, are formulated with only calcium carbonate. Individuals with high blood pressure are advised to avoid excess sodium and may choose to use an antacid without sodium bicarbonate. People with osteoporosis or those who need a calcium supplement may choose an antacid formulated with calcium carbonate. Calcium carbonate, however, if used over long periods of time tends to cause constipation. Thus some antacids contain a combination of calcium carbonate and magnesium hydroxide. This combination tends to overcome the constipation as magnesium hydroxide produces an opposite laxative effect. Magnesium hydroxide, while effective in controlling ulcer pain, has a lower neutralizing capacity and can cause trouble if taken too frequently by people with kidney impairment. In any case, each OTC drug must be taken with caution, and dosage information printed on the label should be strictly followed. In this laboratory activity, two classes of over-the-counter drugs will be analyzed—pain relievers and antacids. Known samples will be tested, and then unknown samples will be identified by comparison with the known samples. This process of determining the identities of unknown substances by comparison to known substances is called qualitative analysis. This can be contrasted to quantitative analysis, the process of determining how much of a given component is present in a sample. Qualitative analysis procedures involve using physical and/or chemical tests, both of which will be performed here. Materials
(for each lab group)
Acetaminophen tablet* Acid Controller Complete®, ¼ tablet† Alka-Seltzer®, ½ tablet† Antacid generic tablet† Aspirin tablet* Bufferin® tablet* Excedrin® tablet* Hydrochloric acid solution, HCl, 0.5 M, 100 drops Ibuprofen tablet* Iron(III) nitrate solution, Fe(NO3)3, 0.2 M, 100 drops Universal indicator solution, 40 drops Unknown OTC antacid sample† Unknown OTC pain reliever sample* Water, distilled or deionized Cotton swabs (for cleaning wells) Mortar and pestle pH indicator paper, 10 pieces Pipets, Beral-type, 4 Reaction plate, 24-well Sheet of white paper Spatula Test tubes, 5 Toothpicks (for stirring), 10 Universal indicator color chart *OTC pain relievers †OTC antacids Prelab Questions
Safety PrecautionsDo not ingest any of the over-the-counter drug samples during this laboratory. The samples are for laboratory use only, have been stored with other non–food-grade laboratory chemicals, and are not meant for human consumption. Hydrochloric acid solution is toxic by ingestion and inhalation and is corrosive to skin and eyes. Iron(III) nitrate solution may be a skin/tissue irritant. Universal indicator solution is a flammable, alcohol-based solution. Avoid contact of all chemicals with eyes and all body tissues. Wear chemical splash goggles, chemical-resistant gloves and a chemical-resistant apron. Wash hands thoroughly with soap and water before leaving the laboratory. ProcedurePart Ia. Known OTC Drug Testing—Pain Relievers
Part Ib. Unknown OTC Drug Testing—Pain Relievers
Part IIa. Known OTC Drug Testing—Antacids
Part IIb. Unknown OTC Drug Testing—Antacids
Student Worksheet PDF |